Chilton Boys
by ofcoursenot121
Summary: This is a definite AU fic set in season one. Rory's going to Chilton, where she meets Paris, Tristan, and Tristan's best friend, Dean Forester.
1. 1 The Lorelais' First Day At Chilton

**rating: **not totally sure yet..pg to pg-13 for language.

**disclaimer: **I don't own Gilmore Girls, never have, probably never will. If I did own Gilmore Girls, lots of things would be different.

**Summary: **This is a definite AU fic set in season one. It's Rory's first day at Chilton and she's already having trouble getting along with the other kids. She runs into Paris Gellar, who hates her already for her good grades and intelligence. She meets Tristan DuGrey, who constantly calls her 'Mary', and she meets Dean Forester, Tristan's best friend. This is a fic basically about what would've happened if Tristan and Dean were friend and both had a thing for Rory.

**A/N: **I'm both a die hard narco and a die-hard trory, so the story could end either ways or have alternate endings. I'm also a Tristan/Louise shipper, so who knows, if Rory ends up with Dean Tristan may end up with Louise...there are lots of possibilities ;)

**A/N 2: **This is also my first fic, so try not to get too nasty in the review. The first chapter or two may be boring, but I promise that if I decide to continue, the updates will be better. I also used a lot of stuff from the second episode of the first season, "The Lorelai's First Day at Chilton" so some dialogue and descriptions/names will be taken from there.

**Chapter One — Lorelai's First Day At Chilton**

**Chapter One — Lorelai's First Day At Chilton **

_Not more than an hour in school and my first day sucks_, Rory Gilmore thought._ It's bad enough I got the 'late girl' label, but it's even worse that Mom came dressed as Daisy Duke to meet the headmaster. Plus, the headmaster has no faith in me. He thinks I can't catch up. I'll just have to prove him wrong, won't I? _

These and many other thoughts were racing through the mind of sixteen-year-old Rory Gilmore as she sat quietly in her first class of the day, listening to the teacher's lecture. She glanced away from the teacher for a moment, while she and a majority of the class noticed a blonde-haired boy entering the classroom with a note in his hand.

The teacher apparently noticed the blonde boy, too, because he stopped teaching to address him.

"Ah, Mr. DuGrey, good of you to join us."

"Sir." The DuGrey boy replied, handing the teacher a slightly crumpled white slip.

"Have a seat, Mr. DuGrey. I'm glad your grandfather is feeling better."

"Thank you, sir, he is." The DuGrey boy said before taking a seat behind a brown-haired boy.

The teacher returned to his lecture, and Rory also returned her attention to the teacher. The DuGrey boy, however, seemed uninterested in the class and leaned forward to speak to the boy in front of him.

"Hey, Dean," he whispered. "Who's that?"

The boy named Dean turned slightly in his seat and looked at the blonde boy.

"Who're you talking about, Tristan?" Dean asked.

Tristan DuGrey pointed to Rory. "Her. Who's she?"

"Oh," Dean said, turning and looking at Rory. "New girl."

"Looks like we got ourselves a Mary, Dean-o." Tristan said with a smirk, and lightly hitting Dean's shoulder.

The bell rang, cutting off the teacher's final words. The students quickly rose, gathered their books and filed out of the classroom, and as Rory headed for the door, the teacher looked up from his desk.

"Miss Gilmore, would you come here please?" he asked.

Rory nodded nervously and approached the teacher, who digs into one of his drawers and pulls out a large black three-ringed binder.

"These are last week's study material, Miss Gilmore." The teacher began. "There will be a test on them tomorrow, but since you're new, I'll allow you to take the make-up exam on Monday. Is that a sufficient amount of time?"

Rory simply nodded, picking up the heavy binder.

"Of course, that's all just an overview. I would advise you to borrow notes from someone. They tend to be more detailed."

_How can anything get more detailed than this?_ Rory thought.

"Oh, sure. I'll get them." She said.

She then exited the classroom. Before she could take more than three steps away from the doorway, a girl with long blonde hair appeared.

"Oh, hi," Rory muttered before colliding with her.

"I'm Paris." The girl said.

"Where'd you come from?" Rory asked.

"I know who you are, too. Lorelai Gilmore from Stars Hollow."

"Actually, you can call me Rory." Rory said politely.

"Are you going out for the Franklin?" Paris asked in a menacing voice.

"The what?"

"The Franklin, the school newspaper, are you going out for it?" Paris said, her patience quickly starting to leave her.

"Um, I don't know. I think I'd like to find my locker first."

"I'm gonna be editor next year."

"That's great for you." Rory said.

"I'm also the top of the class, and I intend to be valedictorian when I graduate." Paris said in a stern tone.

"Okay, I'm gonna go now." Rory said and slightly rolled her eyes.

"You'll never catch up. You'll never beat me. This school and the Franklin are my domain, and don't you forget that." She then turned and hastily walked to her next class.

She's _definitely not lending me her notes…_Rory thought.

Rory began down the hall, pulling out a slip of paper with her locker number on it. She carefully looked at each locker, making sure she hadn't gone too far. As she did this, the same blonde-haired boy from her previous class, Tristan, approached her.

"Hey, Mary." He smirked.

"Me?" Rory said, looking away from the lockers and around the hall for a girl who he may have mistaken her with.

"Yeah, you."

"My name's Rory."

"And I'm Tristan." He said with the same smirk. "So you're new here?"

"Yeah, it's actually my first day."

"Well Remmy's class is pretty rough." Tristan pointed out.

"I noticed. It seemed intense."

"I could loan you my notes if you want." Tristan said, still smirking.

"Really? That would be great!" Rory said, relieved.

"How great?" Tristan grinned, raising an eyebrow.

"Remmy said the notes were pretty important…"

"I could even help you study." Tristan added.

"Um, no thanks." Rory said. "I kind of view studying as a solitary activity."

"Okay. Bye Mary." He smirks once more before leaving.

"It's Rory." She says in an irritated voice.

Tristan DuGrey looked back only once as he walked away from Rory. When he turned back around he was faced with Dean, the boy from Remmy's class.

"You're very good at that." Tristan said. "Almost as good as Paris Gellar."

"Wow, I'm flattered," Dean said sarcastically, beginning to walk alongside Tristan. "So you talked to the new girl?"

"Yeah." Tristan nodded, and then added a grin. "She's a definite Mary. Offered her my notes and told her I could study with her."

"A lot of good that would do," Dean snorted.

"She turned me down, though, on the studying part." Tristan added, a hint of sorrow in his voice.

"Well," Dean said as they came to a classroom doorway. "At least we know for sure that she's smart."

Dean gave his own smirk, but Tristan appeared less amused.

"Sorry, man," Dean began, "But you're not exactly the brains of our dynamic duo."

"I can be just as smart as you, Forrester. I just choose to focus more on the extracurricular activities of school than the actual school, if you know what I mean." With this, Tristan smirked and entered the classroom. Dean simply shook his head.

The clanking of a stuck locker filled the hallway, which was loud to begin with. Rory pulled on the handle of the locker, but with no success. The door wouldn't budge.

_Great, I'm going to be late to my next class because of this stupid thing, _Rory though as she angrily jerked on the handle once more. This time it flew open, sending Rory back a step or two and into another student. The project in the boy's hands fell and crashed to the ground.

Rory's eyes widened as she watched the castle project fall to the floor. She looked at the boy, whose face was well hidden by brown hair.

"I am so sorry," Rory began apologizing but the boy shook his head.

"Don't worry about it." He said softly.

"But I wrecked your project."

He shrugged. "I didn't spend much time on it."

"It doesn't matter, you'll get an incomplete because of me."

"Again, don't worry about it. It wasn't your fault your locker was stuck." He said, and added. "I wish you'd wait a second, though, I was coming over to help you with it."

Rory frowned and opened her mouth to apologize but he held up a hand again. Instead of being angry with her, he picked up the books that she'd dropped along with his own.

"So you're that new girl, right?" He said handing her the books.

"Is it that obvious?" Rory said shyly taking the books and putting them inside the locker.

"It's not that, it's just that my friend and I know practically everyone at this school. We know if there's a new student." He explained.

"Okay, well I'm Rory Gilmore." She said shyly again.

"Dean Forrester." He said with a half-smile.

"Well, Dean," Rory said. "I was wondering if you could tell me where Mrs. Ness' class is?"

"Sure, that's actually my next class." He said turning to look at the classroom across from them. "It's that one right there."

"Oh, thanks," she said walking alongside him across the hallway.

Rory frowned once she saw who else was in this class. Seated in the first row was Paris Gellar, and in the back was Tristan DuGrey. She noticed there were only a few empty seats remaining. She would have to either sit by Tristan or Paris.

_I'll take my chances with Tristan,_ Rory thought as she followed Dean, who sat down in front of Tristan. Rory took the desk beside Dean right when the bell rang.

"Hey, where's your project?" Tristan leaned in and whispered into Dean's ear.

"Don't have it." Dean said in a simple tone.

"You don't have it? You never miss an assignment."

Tristan wanted to press on and get details of Dean's missing project, but Mrs. Ness' voice cut him off.

"Today, class, we will start off where we left Friday, and that is with our projects." Mrs. Ness looked down at a sheet of paper and then directly at Dean. "Mr. Forrester, your project please."

"I don't have it, ma'am." Dean said with slight difficulty.

"Then you shall receive a zero, Mr. Forrester." She said unsympathetically. "I'd expected from you, though."

She looked back down at the list and was about to call on the next person, but Rory stood up, catching the teacher's attention.

"Yes?" She said, slightly annoyed.

"Um, it's my fault he doesn't have his project." Rory said.

"And who are you?" The teacher asked.

"Rory Gilmore." Rory answered.

"I don't have a Rory here, but I do have a Lorelai." The teacher said, uninterested in the news Rory was giving her.

"I go by both, ma'am."

"Well pick one."

"Uh, Rory."

"Well, Rory, you say it's your fault Mr. Forrester doesn't have his project?"

Rory nodded. The teacher continued:

"Well then Miss Gilmore you will help Mr. Forrester re-do his project. You will have until tomorrow. Is that sufficient time?"

Rory nodded once more and lowered herself to sit, but was interrupted.

"Class, while Miss Gilmore is standing, please welcome her." The teacher said looking back down at the sheet of paper.

"Hello, Rory," the class said in unison in a bored and tired voice.

It was Tristan who gave an energetic greeting. "Hello, Mary,"

Dean seemed less enthusiastic than Tristan. As Mrs. Ness moved onto the next person, who happened to be Paris Gellar, he leaned over to Rory.

"Why'd you do that?" He asked.

"I felt bad for ruining your project, so I wanted to make it up to you." Rory said in a whispering tone.

"I told you not to worry about it, though."

"I don't always do what I'm told, you know."

This statement received a smirk from Tristan, who tapped his pen softly on his notebook.

Dean sighed. "Okay, well where do you wanna meet, then?"

"I don't know…" Rory said as she trailed off to think of a location.

"How about your place? You don't live far from here do you?"

"Not very far." She answered.

"Good. I'll get directions after class and I'll see you as soon as I can." Dean said and turned to face the front of the class.

Rory walked across the courtyard of Chilton to where her mother was meant to pick her up. She took off her bookbag and placed it on the ground near her and then tied her hair back. Her eyes searched the courtyard for a place to sit and saw that most of the benches were already occupied. She chose the first of the two vacant benches, which happened to be the closer of the two. She sat with her yellow bookbag between her legs, humming to an unrecognizable song. She was so far deep into her dreamland that she didn't hear the footsteps of someone approaching her, or see the navy blue of his uniform as he stood in front of her. No, she didn't snap out of it until he spoke, then she looked up, blushing with embarrassment.

"Sorry, I didn't see you there." She said sheepishly.

"So…looks like I'm coming home with you." Dean said with a grin.

Rory could imagine what her mother would say, 'First day of school and you're already bringing a guy home?'

"I'll have to check with my mom first, but she'll probably say it's okay." Rory spoke. "You have everything we need, right?"

Dean nodded and then took a seat beside her. A moment later a Jeep pulls up to the courtyard and out comes Lorelai Gilmore, holding two coffees. Rory smiled wide and got up, walking quickly to her mother. When she reached her, she wrapped her arms around her in a monstrous hug.

"Hey, babe, I missed you too." She said as she began to pull away. Rory protested.

"Oh, okay, still hugging."

"Today sucked. I've got so much catching up to do, this one girl already hates me, one of the boys keeps calling me Mary, and I destroyed this other boy's project." Rory said.

"Really? Mary? I can't believe they're still using that." Lorelai said as she headed for the Jeep.

"Why? What's it mean?" Rory asked, not moving.

"It's like the Virgin Mary. It means they think you're a goody-goody." Lorelai explained.

"You're kidding?" Rory wondered. "Well what If I'd looked like a slut?"

"Ah, then they would have added a 'Magdalene' to that." Lorelai said with a wide grin.

"Wow. Biblical insults. This school _is _advanced."

Dean watched from his place on the bench as Rory approached a woman holding coffee and embraced her.

_Must be her mother, _he thought, _But she's pretty young to be a mom. _

He watched as they talked and saw that the mother was heading for the Jeep. He got up and grabbed Rory's bookbag, then made his way over to the two Gilmores.

"This school _is _advanced," he heard Rory say as he approached.

"Oh, hello." Lorelai said once she spotted Dean.

"Hi." Dean replied with a short wave of a hand. "Uh, here."

He handed Rory her bookbag and awkwardly looked from mother to daughter.

"Mom, this is Dean. He's the guy I told you about. I broke his project." She said with a hint of guilt.

"I told her it wasn't a big deal, but she insisted on helping me re-do it." Dean explained to Lorelai.

"That's Rory for ya. Always wanting to help people."

"Mom," Rory said. "Is it okay if Dean comes home with us? We need to get the project done by tomorrow."

"Oh," Lorelai said, her tone of voice changing slightly. "Sure, why not. Hop in Dean, and buckle up."

Dean smiled and entered the Jeep. Rory headed for the passenger side when Lorelai handed her a coffee.

"First day of school and you're already bringing guys home?" Lorelai pointed out.

She turned and entered the car, leaving Rory with the coffee and rolling her eyes.

- - - - - - -

A/N: so that's the end of the first chapter..let me know what you think...


	2. 2 The Dixie Chick

**A/N: **I know this chapter may be a little short, but longer chapters are on the way. This chapter is really that meaningful, it's just there. I'm also sorry for the wait, I've left my notebook, which has all my writings in it, at school. The story will get better later on, and there will be some positive Tristan/Rory interaction, too. I've also decided what ship the story's gonna end with.

**Disclaimer: **I don't own Gilmore Girls or any of the characters, blah blah blah, you know the drill here.

**Chapter Two — The Dixie Chick**

The car ride home was awkwardly silent until they reached Stars Hollow. Upon entrance into the small town, Lorelai held a pretend microphone to her hand, driving slowly through the town.

"Welcome to Stars Hollow, I'm Lorelai Gilmore and I'll be your guide for the day. Let's start by taking a look to our left, where you'll see Luke's Diner." She looks back at Dean. "If you want good coffee, you go there and nowhere else."

"Mom," Rory said. "I don't think a tour of Stars Hollow is necessary."

"Actually, I wouldn't mind seeing the rest of the town." Dean said, and then looked from Rory to Lorelai. "That is, if you two don't mind."

"Are you kidding? I've never gotten to be town tour guide before. This'll be fun!" Lorelai said in a chipper tone. "There's Miss Patty's. We may want to keep you away from there, though."

"Why?" Dean asked.

"Just trust me."

The 'tour' continued for about ten more minutes before they reached the house.

"And welcome to the House of Gilmore." She unbuckled her seatbelt and looked back at Dean with grin. "It has nothing to do with the House of Wax."

"Good, because then I think I would've had to bolt." Dean said, returning the grin.

Lorelai looked over at Rory as Dean exited the car and said quietly, "I like this guy." They both then left the car, Lorelai heading for the front door and Rory standing beside Dean.

"Sorry about the tour." Rory apologized.

"It's okay, I kinda liked it." Dean grinned looking at her. "Your mom seems really cool."

"She is." Rory nodded in agreement.

"You too are pretty close, aren't you?"

"Yeah," Rory said with a nod. "We're best friends."

"Rory! Dean! Come on! I just ordered some pizza, so get inside." Lorelai called from the house.

Dean looks up and says, "Pizza sounds good." Then walks towards the front porch, Rory following shortly afterward.

_Okay, so maybe I was wrong. _Dean thought as he took a bite of his pizza. _Okay, I was completely wrong. This place isn't that bad. Neither is she. She's definitely not like any of the other girls at Chilton._

Dean looked around the living room, where they'd decided to work on the project. On ground beside him stood their castle, which was much more impressive than the one he'd made before. Beside the castle lay his Chilton jacket and tie, and on the table was a large, almost-empty box of pizza.

Dean took another bite of his pizza, and then looked up to see Rory emerging from her room, de-uniformed. He couldn't help but think that she looked pretty.

"Looks like we're almost done." She said, taking a seat next to him on the floor and reaching into the pizza box to grab a slice.

Dean looked at the castle and nodded. "Just need to do some final adjustments and we'll be good."

"And you didn't want me to help you," She took a bite of the pizza.

"I just didn't want you to have to worry about it."

"I would've worried about it even if you hadn't agreed to redoing it. It would've been all my fault that you got a zero on your project."

Just then, Lorelai popped in wearing a wide grin, as always, on her face.

"So you guys are almost done here, huh?" She said, her gaze falling on the completed castle.

"Yeah, just need to do some touch-ups and that sort of stuff." Dean replied.

"Okay, well Rory, I'm going to Luke's and bringing us dinner." She paused. "Should I make it dinner for three?"

"No," Dean said quickly. "I don't want to bother you guys anymore, I'll just eat when I get home."

"You sure?" Rory said looking at him.

"Yeah, I'm sure. Besides, I need to get going soon anyway."

"Do you need a ride?" Lorelai asked.

Dean pulled out a cell phone and shook his head. "No, I'll just call my driver." He held the phone to his ear, rose and walked to the other side of the room as he began talking. Lorelai looked at Rory and said quietly, "Driver?"

Rory simply shrugged and Dean came back.

"He'll be here in less than an hour." He informed the two Gilmores.

"Okay, well I'm gonna go then." Lorelai said, walking out of the room and out of the house.

Dean bent down and began cleaning up the mess they'd made. Rory tucked her hair behind her ears and bends down to help. Before long, the mess is cleaned and the two are sitting on the couch.

"Thanks for the help." Dean said and looked at her.

"Oh, it was no problem." Rory smiled. "I mean, I did break your first one. I'm glad you let me make it up to you."

Dean heard a horn beep from outside and smiled.

"That's my ride." He rose, putting on his Chilton jacket and slinging his bookbag over a shoulder. He then bent down, picked up the castle and smiled at Rory. "I'll see you at school."

Rory nodded. "Yup. School."

Dean soon left and Rory sighed, sitting back down on the couch. After a moment or two, Lorelai entered the house carrying two brown bags with the 'Luke's' logo on them.

"Hey, Dean gone yet?" She asked, holding out one of the bags to her daughter.

"Yeah, he just left," She stuck her head inside and smiled, taking in the smell of Luke's burgers and fries. "Coffee?"

Lorelai held out a cup to her and then took a seat beside her, opening her own bag and pulling out a burger.

"Why were you at Luke's for a half hour?" Rory asked after taking a sip of coffee.

"You know those lines at Luke's." Lorelai said, waving it off.

"Actually, I don't." Rory responded, raising an eyebrow.

Lorelai bit off a large piece of the burger and began chewing slow. Rory grabbed her mother's shoulder and gave it a short shake.

"Stop avoiding the question!" Rory said in an irritated voice.

Lorelai gulped and said, "I'm not, I'm not. Jeez, can't a girl enjoy her burger?"

Rory cast her a look.

"I don't know, Rory," Lorelai began. "I thought you two wanted to be…you know…alone a little bit."

"What's that supposed to mean?" Rory asked. "You wanted me to hook up with a guy I just met?"

"No, of course not. I just thought you two could be friends." Lorelai said, holding up her right hand. "I swear. Besides, you need friends, it's a new school, you need someone to bail you out of tough situations."

Rory crossed her arms over her chest and leaned back on the couch. "I can't believe you thought I wanted to hook up with a boy I first met."

Lorelai scowled and reached into the bag, pulling out a fry and throwing it at Rory.

"Hey!" Rory cried.

Lorelai simply smirked and grabbed the remote, turning on the TV.

_Jeez, Abrams is boring, _thought Tristan DuGrey as he sat slouched in his seat at the back of the room. He lightly tapped the eraser end of his pencil on his Trigonometry book, looking bored out of his mind. He glanced over to the seat next to him, where Dean Forrester sat, leaned forward, his nose buried in his class work. Tristan smirked and looked up at the teacher, who was sitting at her desk dreading a book, glancing up from time-to-time to check for talkers. Tristan looked back at Dean and leaned forward, tapping him lightly on the shoulder.

"So how was it last night?" Tristan asked in a hushed voice.

Dean looked up slowly, his eyes darting from Tristan, to Mrs. Abrams, and to Tristan again.

"What do you mean?" He finally replied.

"You know what I mean." Tristan said, smirking. "You, Mary, her town, her house. How was it?"

"Oh," He said and paused, as if not sure whether he should share the information with his friend or not. Finally he shrugged and said, "It was okay."

"That's it? It was 'okay'?" Tristan asked, raising an eyebrow.

"What else do you want me to say?" Dean asked.

"You didn't make a move or anything"

"Of course I didn't." Dean answered quickly. "That's more your territory, remember, Tristan?"

"Still," Tristan continued. "You didn't try anything?"

"No." Dean said firmly, looking back down at his nearly finished paper.

"So you two seriously just worked on that stupid castle the whole time?"

"Pretty much, yeah." Dean responded, reinforcing his words with a nod.

"Good," Tristan said simply, sitting back in his seat and looking back up at the front of the class.

This response puzzled Dean, who leaned forward and asked, "What do you mean, 'good'?"

"I mean, since you didn't try anything, that means she's fair game." Tristan responded casually with a slight shrug.

"Game? Is that what this is about?"

"You wouldn't mind if I made any moves, though, would you?" Tristan asked.

"So she's just your next conquest, Tristan?" Dean asked in an angry tone.

He shrugged and cast Dean a smirk. "She not _just _a conquest, Forrester. She's gonna be different from the others. She likes to play hard-to-get."

"Unbelievable," Dean muttered shaking his head and sitting back in his seat.

"Look, you're all for that romantic, sappy, commitment stuff. I'm just up for different kinds of relationships," Tristan explained with a lopsided grin.

"Yeah?" Dean said looking over again. "Well you better be careful, Tristan, because if you hurt her, you'll have me to deal with, too."

Tristan snorted and suppressed a laugh. "You? What can you possibly do to _me_? Besides, it's just a girl man. You're gonna let a girl come between us? After we've been friends for years?"

"This girl's different, Tristan," Dean said. "She's just…different."

After a moment, Tristan said, "So you _do_ like her."

"I like her as a friend, Tristan. She seems really nice and she doesn't you to go around messing with her."

Tristan held up his hands, as if surrendering. "Whatever you say, Dean-o, whatever you say."


End file.
